
Vacation rentals with a pool in Block Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Block Island
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Rustic Farmette Studio w/yearround Hot Tub
Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

Detached bungalow w/ private bath
Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

Cozy, serene and private Hamptons home near it all
Come escape to your serene, chic, East Hampton home nestled in nature near all of the best attractions. Make this home your own and enjoy all of the comforts + peace in your own space! Relax by the wood burning fireplace, 80' streaming TV + Chef kitchen. Enjoy the calmness + nature views from all areas of the house. During summer, swim all day, spark up the BBQ + firepit poolside, walk 1 block to waterfront dining/cafe. You'll be 5 minutes to beaches, Main St., dining, shopping+ so much more!

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)
Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

Artist studio in the woods
Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quite, tranquil, relax. As of 1/1/26 booking rate will be $120 per day. Pool $20 seasonal.

Montauk Waterfront Condo w/ Sunset Views
Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf
Spa Resort | Casinos | Heated Seasonal Pool and Hot Tub | Sauna | Fitness Room | Clubhouse | Golf | Restaurants | Heated Massage Chair | Warm Robes and Blankets | Electric Fireplace with Remote| New Serra topper Whether you’re looking to get away or jump in, enjoy this relaxing retreat surrounded by upscale amenities! We’ve done our very best to ensure your stay is comfortable and tranquil, full of necessities and extras, and that there are many nearby options for adventure and fun.

Beauty and the Beach!
Welcome to Beauty and the Beach, where you can come and relax with the whole family or come alone to get away from the busynesses of life! The property is located within an 8 minute walk to Ocean Beach Park and a block away from Alwife cove. With all year recreation. we are located within a short distance to: - Coast Guard Academy -Navy Sub Base -Mohegan Sun -Historic Mystic -Shopping and Great Dining Experiences! -Scenic hiking trails Come and embrace the New England Salty Life!

Perfect New England Getaway has a pool/ hot tub
traditional New England style that is not just a great home, but a great vacation compound with lots of amenities and outdoor living spaces. Enjoy recreational activities on land and sea that abound locally. Mystic, Stonington Borough, Westerly, and Watch Hill are all close IMPORTANT INFORMATION: Please be advised Stonington, CT has a STRICT OUTSIDE Noise ordinance after 10pm that is enforced by the Police. If a report is generated for any reason , you will forfeit your deposit.

Sunset Oasis 2 @ Ocean Beach: Ranch w/ 6 Queen
INSTANT BOOK: Jan 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug WEEKDAY WINTER PACKAGES: Jan - Mar: 4 nights, Mon - Fri $1200 total OR 5 nights, Sun - Fri $1350 total= SEND INQUIRY (Fri & Sat not included, pet fees additional cost) *certain holidays/summer excluded in booking minimums/packages *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Beachfront W/ Hot Tub, Sauna, Pool & Panoramic View
Welcome to the Heart of Somerset! Read our reviews & stay a while! Nestled at the very tip of Somerset on a private dead-end road, this coastal waterfront home is the perfect place for a family retreat, romantic getaway or friends seeking adventure Marvel at the panoramic views and dramatic colors from Sunrise to Sunset. Grab a kayak, or sit back and relax and let the gentle sea breeze wash your worries away!

Cozy private apt 8 mins from UCONN - solar powered
Relax & unwind in this amply sized private studio suite, complete with large seating/tv area & study/desk space. Space comes w/ 2 beds (1 queen, 1 full sized pull out futon couch) a full private bath, mini-fridge, cooktop, microwave, dishware, & utensils. Beautiful rural wooded area with numerous hiking trails nearby. Longer term rentals may be considered starting from Summer of 2025
Popular amenities for Block Island rentals with a pool
House rentals with a pool

Casino Wine Down House with Winter Igloo

Private & Pristine with Pool and Kid’s Playard

Casa Greenport

Cheerful East Hampton home with Pool

Mini Estate Walk to Ocean & Town

mid century ranch style house on farmland

3BR/3.5BA: East Hampton, Heated Pool, Hot Tub

The Hamptons Casita: Modern Elegance Meets Cozy
Condo rentals with a pool

Villa Flora @ Norwich Inn & Spa

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Montauk Royal Atlantic Beach Resort North

2 BR Waterfront Autumn Escape in Wine Country

Beautiful Waterview Condo on the North Fork of LI

The Vacay Villa

Peaceful Oasis steps from Mohegan Sun

Beautiful Condo on the Ocean Bluffs
Home rentals with a private pool
Enchanting Home with Large Decks and Heated Pool

East Hampton Ranch with Access to Clearwater Private Beach

Explore the Water & Woods at a Relaxing Retreat
Saltbox with Separate Poolhouse in Northwest Woods
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Bed and breakfasts Block Island
- Hotel rooms Block Island
- Rentals with a fireplace Block Island
- Cottage rentals Block Island
- Family-friendly rentals Block Island
- Beach house rentals Block Island
- Rentals with a patio Block Island
- Pet-friendly rentals Block Island
- Rentals with a fire pit Block Island
- Rentals with breakfast Block Island
- House rentals Block Island
- Waterfront rentals Block Island
- Rentals with a washer and dryer Block Island
- Rentals with outdoor seating Block Island
- Rentals with beach access Block Island
- Beachfront rentals Block Island
- Apartment rentals Block Island
- Condo rentals Block Island
- Rentals with pools New Shoreham
- Rentals with pools Washington County
- Rentals with pools Rhode Island
- Rentals with pools United States
- Foxwoods Resort Casino
- Brown University
- Charlestown Beach
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Easton Beach
- Roger Williams Park Zoo
- Second Beach
- The Breakers
- Mohegan Sun
- South Shore Beach
- Bonnet Shores Beach
- Mystic Seaport Museum
- East Matunuck State Beach
- Fort Adams State Park
- Burlingame State Park
- Salty Brine State Beach
- Orient Beach State Park
- Narragansett Town Beach
- East Hampton Main Beach
- Easton's Beach
- Wölffer Estate Vineyard
- Bluff Point State Park




